At a Glance
- Tasks: Lead transformative operational projects and architect AI-driven solutions for scalable systems.
- Company: Trilogy, a dynamic tech company known for innovation and operational excellence.
- Benefits: Competitive pay of $200,000/year, remote work, and opportunities for rapid career growth.
- Other info: Join a team that values speed, innovation, and direct execution without red tape.
- Why this job: Make a significant impact by driving automation and efficiency in a fast-paced environment.
- Qualifications: 5+ years in operational leadership, Python automation skills, and experience with LLM APIs.
This position is designed for operators capable of constructing and reconstructing scalable systems from the ground up. Operational excellence at Trilogy is not optional—it is our competitive edge. We move quickly to acquire software companies and scale them at an accelerated pace. To sustain this velocity, we require executives who can architect and implement lean, automated infrastructure—not those who solve problems by expanding headcount.
You will take full ownership of end-to-end operational transformations spanning our worldwide portfolio. Your work may involve redesigning offboarding workflows for 1,200+ employees after acquisition, replacing legacy platforms like Jira and Salesforce with AI-driven agents, or creating automations that cut thousands of manual hours. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that allow you to concentrate on results.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We function with fewer hierarchies, shorter cycles, and more demanding standards than conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating red tape or overseeing inflated teams. We do not engage in static operations. We do not delegate transformation externally. And we do not hire individuals who require approval or extensive teams to produce results. We are seeking a select group of technically proficient, execution-oriented leaders who leverage automation for force multiplication and treat speed as a strategic asset. If this describes you—this environment will suit you well.
What You Will Be Doing
- Driving high-stakes operational projects including M&A integration, enterprise system replacement, and organization-wide transitions
- Architecting and delivering automations that displace CRM and task management platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
- Owning initiatives from initial diagnosis through final deployment, applying tested playbooks and exercising executive judgment
- Successfully completing a practical technical assessment to validate your capability to design and build AI-centric solutions
What You Won't Be Doing
- Overseeing large teams or depending on multiple layers of personnel to accomplish objectives
- Participating in prolonged alignment sessions or waiting for consensus before taking action
- Handing off critical work to IT departments or third-party vendors—you will design and implement solutions directly
- Running steady-state operations—this role centers on transformation and rapid execution
Key Responsibilities
- Architect and implement AI-driven operational frameworks that remove manual effort, reduce complexity, and enable scalable execution throughout Trilogy's global software portfolio.
Basic Requirements
- 5+ years of operational leadership in business operations
- Experience delivering presentations to C-suite executives
- Experience building automation in Python and integrating with LLM APIs
- Experience deploying production-grade automations using Cursor, Windsurf, MCP, or comparable tools
- Ability to work remotely with a minimum of 6 hours overlap with the CST time zone
About Trilogy
Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer‑facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.
Working with us
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.
Operations AI Lead, Trilogy (Remote) - $200,000/year USD employer: Crossover
Trilogy is an exceptional employer that champions operational excellence and innovation, providing a dynamic remote work environment where talented individuals can thrive. With a focus on rapid execution and minimal hierarchy, employees are empowered to take ownership of transformative projects, leveraging cutting-edge technology and automation to drive significant impact across a diverse portfolio of software businesses. The company fosters a culture of growth and collaboration, ensuring that every team member has the opportunity to develop their skills and advance their careers while contributing to meaningful change.
StudySmarter Expert Advice🤫
We think this is how you could land Operations AI Lead, Trilogy (Remote) - $200,000/year USD
✨Tip Number 1
Network like a pro! Reach out to folks in your industry on LinkedIn or at events. A personal connection can often get you noticed faster than a CV.
✨Tip Number 2
Show off your skills! Create a portfolio or a project that highlights your expertise in automation and AI. This gives potential employers a taste of what you can do.
✨Tip Number 3
Prepare for the interview by practising common questions, but also be ready to discuss how you’d tackle real-world problems. Think about how you’d implement solutions using Python and LLM APIs.
✨Tip Number 4
Apply through our website! It’s the best way to ensure your application gets seen. Plus, it shows you’re serious about joining our team at Trilogy.
We think you need these skills to ace Operations AI Lead, Trilogy (Remote) - $200,000/year USD
Some tips for your application 🫡
Show Your Operational Excellence:When you’re crafting your application, make sure to highlight your experience in operational leadership. We want to see how you've driven transformations and implemented scalable systems in your previous roles. Remember, operational excellence is our competitive edge!
Be Specific About Your Technical Skills:Don’t just list your skills—show us how you’ve used Python, LLM APIs, and tools like Cursor or Windsurf in real projects. We’re looking for execution-oriented leaders, so give us examples of how you’ve architected automations that made a difference.
Keep It Concise and Impactful:We appreciate clarity and brevity. Make your application easy to read and straight to the point. Use bullet points where possible to outline your achievements and responsibilities. We want to see your impact without wading through fluff!
Apply Through Our Website:We encourage you to apply directly through our website. This ensures your application gets to the right people quickly. Plus, it’s the best way to stay updated on your application status. Don’t miss out on this opportunity—apply now!
How to prepare for a job interview at Crossover
✨Know Your Tech Inside Out
Make sure you’re well-versed in Python and LLM APIs, as these are crucial for the role. Brush up on your experience with tools like Cursor, Windsurf, and MCP, and be ready to discuss specific projects where you've implemented these technologies.
✨Showcase Your Operational Excellence
Prepare examples that highlight your ability to drive operational transformations. Think about times when you’ve architected solutions that improved efficiency or reduced manual processes, and be ready to explain your thought process and the results achieved.
✨Demonstrate Speed and Agility
Trilogy values rapid execution, so be prepared to discuss how you’ve made quick decisions in high-stakes situations. Share instances where you’ve successfully led projects without getting bogged down in red tape or excessive approvals.
✨Prepare for a Practical Assessment
Expect a technical assessment to validate your skills. Practice designing and building AI-centric solutions ahead of time, and be ready to showcase your problem-solving abilities in real-time during the interview.
